Water → HCID 20145029, compound

HRID 1906003Notes

Reaction equation

HRID 1906003 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]3[CH:18]=2)=[C:6]([CH3:8])[N:7]=1.[BrH:19].[NH+]1C=CC=CC=1.O.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O1CCCC1>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]3[C:18]=2[Br:19])=[C:6]([CH3:8])[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20144964HCID 20144964, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 20145029HCID 20145029, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-methylamino-4-methylthiazol-5-yl)-7-methylimidazo[1,2-a]pyridine (1.92 g) in a mixture of acetic acid (14 ml) and tetrahydrofuran (10 ml) was added pyridinium hydrobromide perbromide (2.6 g) at ambient temperature and the mixture was stirred for an hour. The reaction mixture was poured into water and the resultant aqueous solution was adjusted to pH 7.5 with saturated potassium carbonate. The product was extracted with chloroform and the extract was dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a crystalline residue, which was recrystallized from a mixture of methylene chloride and diethyl ether to give 2-(2-methylamino-4-methylthiazol-5-yl)-3-bromo-7-methylimidazo[1,2-a]-pyridine (2.2 g).

Workup

  1. extractionThe product was extracted with chloroform
  2. dry with materialthe extract was dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto afford a crystalline residue, which
  5. customwas recrystallized from a mixture of methylene chloride and diethyl ether

Sources & evidence

ORD record
ord-06a849614df4468fba5ebfb4a5c044da
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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